The present invention relates to 1-phenylpenten-4-one-1 and methyl homologues thereof having the generic structure: ##STR2## wherein one of R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is hydrogen or wherein both R.sub.1 and R.sub.2 are hydrogen and uses thereon in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles.
There has been considerable work performed relating to substances which can be used to impart (or alter, modify or enhance) fragrances to (or in) perfume compositions, perfumes, colognes or perfumed articles. These substances are used to diminish the use of natural materials some of which may be in short supply and/or to provide more uniform properties in the finished product.
Green, elang, fruity, floral, rosey, animalic, opoponax, myrrh, mushroomy, hyacinth and lavender aroma nuances are particularly desirable in many types of perfume compositions, perfumes and perfumed articles, e.g. solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, drier-added fabric softener articles, hair preparations and perfumed polymers.
Aryl alkenones and aryl alkadienones are known in perfumery for augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles. Thus, Arctander "Perfume and Flavor Chemicals (Aroma Chemicals)" Volumes I and II discloses the use in augmenting or enhancing perfumes of:
benzylidene acetone at monograph 318 of Volume I PA0 3-methyl-4-phenyl-3-buten-2-one at monograph 2171 of Volume II PA0 phenyl vinylethylene methylketone at monograph 2609 of Volume II thusly:
__________________________________________________________________________ 318: BENZYLIDENE ACETONE Methyl cinnamyl ketone. Sweet, but rather pungent odor with a Methyl styryl ketone. creamy-floral note. Benzal acetone. Occasionally used in perfumery for Sweet "Benzylidene ketone" (confusing name). Pea (used to be a "must" in this type of frag- 4-Phenyl-3-buten-2-one. rance), in Appleblossom, etc., often in com- Cumaranol. bination with Neroli and Hyacinth bases. Exists in cis- and trans-form. (Commercial Also used in flavors, particularly in Choco- product is cis-isomer). late, Cocoa, Cherry, Fruit, Nut, Vanilla, etc.- Note: Do not confuse with Benzyl acetone. but usually at very low concentration. Con- ##STR3## centration in finished product will rarely ex- ceed 0.2 to 0.5 ppm. Prod. by Claisen condensation of Benz- aldehyde and Acetone. G.R.A.S. F.E.M.A. No. 2881. Note: This ketone is repeatedly reported in trade literature as being strongly skin-irritat- ing. It may be that its acceptance in food is Yellowish plate crystals. M.P. 42.degree. C. (cis- approved only because of very low use-con- isomer). M.P. 4.degree. C. (trans-isomer). centration. Sp.Gr. 1.04. B.P. 262.degree. C. Insoluble in water, 4-19; 4-22; 5-165; 26-418; 30-179; 31-84; soluble in alcohol and oils. Also soluble in 95-170; 96-150; 100-139; B-VII-364; sulfuric acid solution. __________________________________________________________________________ 2171: 3-METHYL-4-PHENYL-3-BUTEN-2-ONE Benzylidene methyl ethyl ketone. alpha-Methylcinnalylidene methylketone. Benzylidene acetone methyl. alpha-Methyl-alpha-benzalacetone. "Malvone" (Agfa). "Lavandozon" (Haarmann & Reimer). ##STR4## Pale yellowish crystals. This ketone finds some use in flavor com- Almost insoluble in water, soluble in alcohol positions, although there are several chemicals and oils. of similar and better type available. Traces Sweet, fruity-caramellic, berry-like odor of are used in many berry compositions, imitation good tenacity. Cherry, Vanilla and in Nut complexes. The effect is overall milder than that of The concentration will normally be as low Benzylidene acetone. as 0.5 to 3 ppm in the finished product. Sweet fruity, Cherry-Plum-like taste in Prod.: by condensation of Benzaldehyde dilutions below 10 ppm. Somewhat bitter at with Methyl ethyl ketone. higher concentrations. G.R.A.S. F.E.M.A. No. 2734. Trace amounts give interesting effects in 86-89; 4-19; Lavender fragrances. __________________________________________________________________________ 2609: PHENYL VINYLETHYLENE METHYLKETONE Cinnamylidene acetone. Warm-herbaceous, green-floral and very Phenyl-1,3-butadiene methylketone. tenacious odor. 6-Phenyl-3,5-hexadien-2-one. This material, rarely offered under its proper 1-Phenylhexa-1,3-dien-5-one. name, and often confused with the natural Chrystanthone. component of Chrysanthemum, is occasion- Note: This material is not identical to the ally used as a fixative and floral-herbaceous "Chrysanthone" identified as component of blender/modifier in perfume compositions. Chrysanthemum (plant). Although it seems to be absolutely unknown ##STR5## in many perfumery circles, it is very highly appreciated by others, and it can give quite unique effects when used with experience. It gives very pleasant notes with Mimosa ab- solute, Ylang, Opopanax, Patchouli, etc. in the heavy Oriental-floral type. White crystals. M.P. 68.degree. C. Prod.: by condensation of Cinnamic alde- Practically insoluble in water, poorly soluble hyde with Acetone. in cold alcohol, soluble in hot alcohol and 36-1255; 68-990; 103-274; 163-65; most oils. __________________________________________________________________________
Cyclic unsaturated compounds bonded to 1-pentenoyl moieties are also known for use in augmenting or enhancing the aroma of perfumes, perfume compositions and perfumed articles. Thus, U.S. Pat. Nos. 4,264,467 issued on Apr. 28, 1981, 4,289,659 issued on Sept. 15, 1981 and 4,147,672 issued on Apr. 3, 1979 disclose compounds having the structures: ##STR6## and the genus of compounds having the structure: ##STR7## wherein the dashed lines represent carbon-carbon single bonds or one or two carbon-carbon double bonds.
None of the prior art disclosures, however, disclose the use in perfumery of the genus of compounds defined according to the structure: ##STR8## wherein one of R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is hydrogen or wherein both R.sub.1 and R.sub.2 are hydrogen.
The compound having the structure: ##STR9## is a known compound and is disclosed at Beilstein H-373; EII 298 (abstracting J. M. Chem. Soc. Volume 58 (1936) 892 and J. M. Chem. Soc. Volume 60 (1938) 1905, 1911, disclosures of which are incorporated herein by reference).